Homes with Pools for Sale in Orange County, NY

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ABOUT THIS HOME
Home with a Pool for sale in Orange County, NY:
Welcome to 747 Oakland Valley Road in Cuddebackville, NY—a rare Neversink Riverfront gem that seamlessly blends rustic charm with thoughtful modern updates. Tucked away on a full acre of land in the Port Jervis School District, this enchanting 4-bedroom, 2-bath two-story home offers just under 1,400 square feet of inviting living space, perfect for year-round living or as a weekend retreat. Pull into the paved driveway, spacious enough to accommodate multiple vehicles and even your river boat, and be greeted by the oversized, two-car pull-through garage—an ideal setup for hobbyists, outdoor enthusiasts, or anyone in need of serious storage space. A quaint front yard and front po

$299,000

4 beds2 baths1,352 sq ft

747 Oakland Valley Rd, Cuddebackville, NY 12729

Neversink riverfront • Paved driveway • Private patio

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Home with a Pool for sale in Orange County, NY:
Come and experience the extraordinary, unparalleled newly renovated opportunity that awaits you at 443 Rye Hill! This is a chance you certainly don't want to overlook. Nestled within stunning grounds and encircled by lush, green trees, this property offers a serene retreat where you can fully immerse yourself in the beauty of nature. As you step inside, you're greeted by a charming foyer. Ascending further, you discover an expansive dining room complemented by a cozy fireplace, perfect for intimate gatherings and family meals. Continuing onward, the home unveils a breathtaking kitchen, equipped with an abundance of cabinets and all appliances. The home boasts numerous spacious and bright ro

$499,000

5 beds2.5 baths2,456 sq ft

443 Rye Hill Rd, Monroe, NY 10950

Cozy fireplace • Charming foyer • Newly renovated

Listing by MK Realty Inc

ABOUT THIS HOME
Home with a Pool for sale in Orange County, NY:
Find your space to breathe at 254 Shoddy Hollow Road in Otisville! This charming 3-bedroom, 2-bath ranch blends country comfort with everyday convenience. You’ll love the spacious kitchen, formal dining room, and cozy living room with a fireplace insert — perfect for gathering on cool evenings. The primary suite offers a relaxing retreat with its own full private bath, while the large yard and two oversized pole barns give you all the room you need for storage, projects, or play with compressors included. Tucked away in a peaceful setting but just a short drive to town, this home offers the best of both worlds — space, comfort, and a sense of home. Two separate driveways,

$549,000

3 beds2 baths1,674 sq ft

254 Shoddy Hollow Rd, Otisville, NY 10963

Cozy living room • Formal dining room • Spacious kitchen

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Home with a Pool for sale in Orange County, NY:
DEER RUN! Low Taxes! End Unit! 2 Bedrooms! 2 Full Bathrooms! 3 Car Garage! Master Bedroom Suite with Walk In Closet! Over Sized Living Room/Dining Room! Hard Wood Floors! Recessive Lighting! Central Air! Clubhouse! Pool! Close to Major Highways, Buses, Trains & Shopping!

$259,900

2 beds2 baths1,291 sq ft

118 Deer Ct Dr Bldg 5, Middletown, NY 10940

$417 HOA • 3 garage spots • Community pool

Listing by ARC Realty 1 in Sales

ABOUT THIS HOME
Home with a Pool for sale in Orange County, NY:
Calling all investors. This home is in the Country Club section of Maybrook! End unit! This home will require some work, but has it's own in-ground pool! Spacious bedrooms and living spaces. Off street parking. Close to 84, shopping, parks and all schools within the district. With some updating, this home will be fabulous! Low taxes and no HOA. Must have cash or rehab loan. Short sale- 3rd party approval

$215,000

3 beds1.5 baths1,400 sq ft

204 Chrystal Dr, Maybrook, NY 12543

Close to parks • In-ground pool • Close to schools

Listing by Hudson Valley Home Connection

Property at 51 West Main St, Port Jervis, NY 12771, 4 beds, 3 baths

$419,000

4 beds3 baths3,410 sq ft

51 West Main St, Port Jervis, NY 12771

Listing by Curasi Realty, Inc.

Property at 10 Rumsey St, Port Jervis, NY 12771, 3 beds, 1 bath

$200,000

3 beds1 bath1,396 sq ft

10 Rumsey St, Port Jervis, NY 12771

Listing by Orange West Realty

Property at 657 Jersey Ave, Greenwood Lake, NY 10925, 2 beds, 3 baths

$850,000

2 beds3 baths2,500 sq ft

657 Jersey Ave, Greenwood Lake, NY 10925

Listing by Our House Real Estate Group

Property at 1 Stahl Way, Monroe, NY 10950, 4 beds, 3.5 baths

$919,900

4 beds3.5 baths3,028 sq ft

1 Stahl Way, Monroe, NY 10950

Listing by Weichert Realtors

Property at 2768 State Route 207, Campbell Hall, NY 10916, 4 beds, 1.5 baths

$465,000

4 beds1.5 baths2,460 sq ft

2768 State Route 207, Campbell Hall, NY 10916

Listing by BHHS Hudson Valley Properties

Property at 204 Ruby Ct, Highland Mills, NY 10930, 2 beds, 2 baths

$314,900

2 beds2 baths1,086 sq ft

204 Ruby Ct, Highland Mills, NY 10930

Listing by Weichert Realtors

Property at 31 Allison Ave, Newburgh, NY 12550, 3 beds, 1.5 baths

$289,000

3 beds1.5 baths1,488 sq ft

31 Allison Ave, Newburgh, NY 12550

Listing by YourHomeSold Guaranteed Realty

Property at 135 N Orange, Port Jervis, NY 12771, 3 beds, 3 baths

$399,000

3 beds3 baths1,936 sq ft

135 N Orange, Port Jervis, NY 12771

Listing by Homes By Yara Realty Group LLC

Property at 172 Ridge Rd, Highland Mills, NY 10930, 3 beds, 2 baths

$534,999

3 beds2 baths1,600 sq ft

172 Ridge Rd, Highland Mills, NY 10930

Listing by Keller Williams Realty

Property at 383 Route 32, Central Valley, NY 10917, 4 beds, 3 baths

$799,000

4 beds3 baths2,076 sq ft

383 Route 32, Central Valley, NY 10917

Listing by Rock Realty Group USA Inc

Property at 7 Felter Hill Rd, Monroe, NY 10950, 3 beds, 3 baths

$549,900

3 beds3 baths3,172 sq ft

7 Felter Hill Rd, Monroe, NY 10950

Listing by River Realty Services, Inc.

Property at 45 E Green Rd, Rock Tavern, NY 12575, 3 beds, 2 baths

$399,000

3 beds2 baths1,310 sq ft

45 E Green Rd, Rock Tavern, NY 12575

Listing by Christie's Int. Real Estate

Property at 28 Spring St, Middletown, NY 10940, 4 beds, 2 baths

$329,000

4 beds2 baths1,696 sq ft

28 Spring St, Middletown, NY 10940

Listing by Howard Hanna Rand Realty

Property at 10 Damian Ct, Chester, NY 10918, 11 beds, 6.5 baths

$1,375,000

11 beds6.5 baths4,327 sq ft

10 Damian Ct, Chester, NY 10918

Listing by MS Realty Group USA, Inc

Property at 3 Warwick Gardens Dr, Warwick, NY 10990, 4 beds, 2 baths

$599,000

4 beds2 baths1,630 sq ft

3 Warwick Gardens Dr, Warwick, NY 10990

Listing by Ridge & Valley RE Corp

Property at 15 Lindentree Ln, Middletown, NY 10940, 3 beds, 2.5 baths

$489,900

3 beds2.5 baths1,827 sq ft

15 Lindentree Ln, Middletown, NY 10940

Listing by Real Estate Circuit Inc

Property at 23 West Meadow Way, Warwick, NY 10990, 4 beds, 2.5 baths

$920,000

4 beds2.5 baths2,969 sq ft

23 West Meadow Way, Warwick, NY 10990

Listing by BHG Real Estate Green Team

Property at 220 Oxford Rd, Chester, NY 10918, 4 beds, 3.5 baths

$699,000

4 beds3.5 baths3,472 sq ft

220 Oxford Rd, Chester, NY 10918

Listing by Exit Realty Venture

Property at 5 Stoll St, Port Jervis, NY 12771, 4 beds, 2 baths

$299,000

4 beds2 baths2,354 sq ft

5 Stoll St, Port Jervis, NY 12771

Listing by Avion

Property at 797 Route 284, Westtown, NY 10998, 2 beds, 1 bath

$260,000

2 beds1 bath1,240 sq ft

797 Route 284, Westtown, NY 10998

Listing by Christie's Int. Real Estate

Property at 7 Laura Ln, Otisville, NY 10963, 3 beds, 1.5 baths

$374,999

3 beds1.5 baths7 sq ft

7 Laura Ln, Otisville, NY 10963

Property at 8 Brian Ct, Salisbury Mills, NY 12577, 4 beds, 2.5 baths

$612,000

4 beds2.5 baths3,784 sq ft

8 Brian Ct, Salisbury Mills, NY 12577

Listing by AI Realty Brokerage LLC

Property at 221 Woodlands Dr, Tuxedo Park, NY 10987, 3 beds, 2.5 baths

$599,000

3 beds2.5 baths1,713 sq ft

221 Woodlands Dr, Tuxedo Park, NY 10987

Listing by Keller Williams Valley Realty

Property at 310 Oak Ln, Newburgh, NY 12550, 3 beds, 2 baths

$799,000

3 beds2 baths1,440 sq ft

310 Oak Ln, Newburgh, NY 12550

Listing by Compass Greater NY, LLC

Property at 28 Sutherland Dr, Highland Mills, NY 10930, 4 beds, 2.5 baths

$729,000

4 beds2.5 baths2,400 sq ft

28 Sutherland Dr, Highland Mills, NY 10930

Listing by Howard Hanna Rand Realty

Property at 312 County Route 1, Warwick, NY 10990, 3 beds, 2.5 baths

$1,370,000

3 beds2.5 baths3,402 sq ft

312 County Route 1, Warwick, NY 10990

Listing by Tuxedo Hudson Realty Corp

Property at 208 Oakland Ave, Monroe, NY 10950, 4 beds, 4.5 baths

$929,000

4 beds4.5 baths3,410 sq ft

208 Oakland Ave, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 234 Concord Ln #234, Middletown, NY 10940, 1 bed, 1 bath

$155,000

1 bed1 bath735 sq ft

234 Concord Ln #234, Middletown, NY 10940

Listing by Weichert Realtors

Property at 2 Cedar Rd, Highland Mills, NY 10930, 4 beds, 1 bath

$447,000

4 beds1 bath1,225 sq ft

2 Cedar Rd, Highland Mills, NY 10930

Listing by Z Wisdom Realty Inc.

Property at 120 W Main St, Port Jervis, NY 12771, 3 beds, 2 baths

$375,000

3 beds2 baths1,890 sq ft

120 W Main St, Port Jervis, NY 12771

Listing by Keller Williams Realty

Property at 14 Bellevue Rd, Newburgh, NY 12550, 4 beds, 2 baths

$399,999

4 beds2 baths1,200 sq ft

14 Bellevue Rd, Newburgh, NY 12550

Listing by Weichert Realtors

Property at 568 Gulliver Ter, Walden, NY 12586, 3 beds, 2 baths

$99,500

3 beds2 baths924 sq ft

568 Gulliver Ter, Walden, NY 12586

Listing by Century 21 E & M Williams Rlty

Property at 86 Gardnertown Rd, Newburgh, NY 12550, 3 beds, 1 bath

$399,000

3 beds1 bath1,582 sq ft

86 Gardnertown Rd, Newburgh, NY 12550

Listing by Keller Williams Realty Partner

Property at 5 Case Ct, Monroe, NY 10950, 3 beds, 2.5 baths

$565,000

3 beds2.5 baths1,954 sq ft

5 Case Ct, Monroe, NY 10950

Listing by RE/MAX Benchmark Realty Group

Property at 223 Margo St, New Windsor, NY 12553, 3 beds, 1.5 baths

$410,000

3 beds1.5 baths1,691 sq ft

223 Margo St, New Windsor, NY 12553

Listing by John J Lease REALTORS Inc

Property at 27 Cherrywood Dr, Goshen, NY 10924, 3 beds, 1.5 baths

$489,000

3 beds1.5 baths1,284 sq ft

27 Cherrywood Dr, Goshen, NY 10924

Listing by Keller Williams Hudson Valley

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Based on information submitted to the MLS GRID as of Tue Dec 02 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Orange County

There are currently 1192 homes with pools for sale in Orange County at a median listing price of $499K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Orange County stay on the market for 62 days and receive 3 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 267 homes have been sold in Orange County. In addition to houses in Orange County, there were also 128 condos, 3 townhouses, and 119 multi-family units for sale in Orange County last month. Find your dream home in Orange County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Orange County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Orange County. If you're looking to sell your home in the Orange County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Orange County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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